4-CHLORO-3-METHYLBENZALDEHYDE Chemical Properties

Melting point:

27-28°C

Boiling point:

115°C 27mm

Density 

1.195±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

White to light yellow Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-51-41-37/38

Safety Statements 

26-36/37/39-39

HS Code 

2913000090

4-CHLORO-3-METHYLBENZALDEHYDE Usage And Synthesis

Uses

4-Chloro-3-methylbenzaldehyde is a reactant used in the preparation of pyrrolidine Ureas as C-C chemokine receptor 1 (CCR1) antagonists.

Synthesis

1) Synthesis of intermediate A33-2: Phosphorus oxychloride (POCl3, 18.3 mL, 200 mmol) was added to a 100 mL two-necked flask and stirred 100 times. 2-Methyl-2-butenenitrile (A33-1, 10.43 g, 70%, 90 mmol) was dissolved in N,N-dimethylformamide (DMF, 15.4 mL, 200 mmol) and slowly added dropwise to the above solution. After the dropwise addition, the reaction was stirred at 110°C for 24 hours. After the reaction was completed, it was cooled to room temperature and the reaction mixture was slowly diluted with dichloromethane (100 mL) and then poured into ice water. The aqueous phase was extracted with dichloromethane (100 mL x 3), the organic phases were combined and washed with water. The organic phase was then washed with saturated saline (200 mL x 3), dried over anhydrous sodium sulfate, filtered to remove the desiccant, and the solvent was removed by rotary evaporation. The residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate=10:1) to give a white solid product (2.9 g, 21% yield).

References

[1] Patent: CN105254613, 2016, A. Location in patent: Paragraph 0246; 0247; 0248

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